Acetic Acid → 3,7-Diazabicyclo(3.3.1)nonane

HRID 1823330ノート

反応式

HRID 1823330 の反応式
C[CH:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=C[CH:4]=1.C=O.C(O)(=O)C.[CH2:16]([N:23]1CCC(=O)CC1)C1C=CC=CC=1>CO>[CH2:8]1[CH:7]2[CH2:6][NH:9][CH2:2][CH:3]1[CH2:4][NH:23][CH2:16]2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 74081-PhenethylamineHCID 192201-Benzyl-4-piperidone

生成物 1

HCID 1927203,7-Diazabicyclo(3.3.1)nonane

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of α-methylbenzylamine (10.7 g, 0.088 mol), paraformaldehyde (21.1 g, 0.703 mol), acetic acid (10.2 mL, 0.179 mol) and 1-benzyl-4-piperidone (16.7 g, 0.088 mol) in MeOH (418 mL) was heated at reflux overnight. Upon cooling to room temperature the solvents were removed in vacuo. Water (700 mL) and KOH pellets (11.7 g, 0.209 mol) were added and the mixture was extracted with 3×150 mL CH2Cl2. The organic layer was dried (K2CO3), filtered and the solvent was removed in vacuo. The yellow residues were triturated with hexane and the combined organic solvents were concentrated to provide bispidine (1) as a crude yellow oil (26.7 g, 90%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customwere removed in vacuo
  4. additionWater (700 mL) and KOH pellets (11.7 g, 0.209 mol) were added
  5. extractionthe mixture was extracted with 3×150 mL CH2Cl2
  6. dry with materialThe organic layer was dried (K2CO3)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe yellow residues were triturated with hexane
  10. concentrationthe combined organic solvents were concentrated

出典と根拠

ORDレコード
ord-2c85c2b1bd86484192e0d660fb7aef68
出典データセット
uspto-grants-2006_05
特許番号
US07038054B1

反応ノート

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